Taylor Swift, Jay Leno, Conan

For a small state, Rhode Island has a lot of grand real estate.

A playground for the rich and famous during the Gilded Age, the shorelines are dotted with mansions. Some of them are tourist attractions, but others are still functioning (vacation) homes for today’s elite.

From the mansions of Newport to the more casual homes in Watch Hill and Warwick, here are five homes that are owned by some well-known celebrities.

$400K is the median selling price in RI:But what kinds of house does it actually buy?

1. Taylor Swift’s $17 million house in Westerly

A big star, with a big reputation, Taylor Swift is arguably the most well-known of Rhode Island’s celebrities. Dubbed the “Holiday House,” Swift bought the Watch Hill mansion in 2013, complete with an Olympic-sized swimming pool and a past that ties it to the Standard Oil fortune. The songwriter spun the story of the house’s past — and the divorcee who lived there, Rebekah Harkness — into the song “Great American Dynasty” in her eighth studio album Folklore.

In this era, the house pops up on social media often in the summertime. It was the spot of her much-talked-about 4th of July parties from 2013 to 2017, and this past summer Blake Lively posted photos of herself and Ryan Reynolds visiting.

2. Conan O’Brien’s vacation home in Westerly

Conan O'Brien

It’s well known around these parts that comedian Conan O’Brien is a New Englander, with a Boston, Irish Catholic background and a Harvard degree to boot. Slightly less known is that his family has a vacation home in Watch Hill, which the Conan host bought in 1997.

In 2014, there was a kerfuffle involving Westerly putting his house up for auction due to him owe $8,000 in back taxes, but it was quickly resolved when the taxes were paid. O’Brien’s publicist said it was due to a clerical error. At the time, the house was worth $723,000.

These days, people sometimes spot him walking around Westerly during the summertime.

3. Jay Leno’s Gilded Age mansion on Ocean Drive in Newport

Jay Leno sits behind the wheel of a 1937 Bentley in front of Seafair, his Newport mansion.  Parked in the background, from left, are a 1930 Packard Dual-Cowl Phaeton, a 2013 Mercedes-Benz SLS AMG Black Series and a 2014 Bugatti Veyron, all on loan from the Audrain Automobile Museum. [Dave Hansen Photography]

Comedian Jay Leno isn’t necessarily known for being a gilded mansion kind-of-a-guy, but he has one — Seafair on Ocean Drive in Newport.

Leno lives primarily on the West Coast, but, like Conan, he was born and raised in Massachusetts and has family on the East Coast. On a visit to Newport in 2017, he was driving with his wife along Ocean Drive, saw the house they had once admired 30 years ago, pulled over, found out it was for sale, and bought it with everything inside for $15 million. When telling this story to a USA Today network reporter in 2019, he said getting the house with everything in it was a big selling point, as it ensured he would never have to spend time thinking about fabric swatches, which he described as a nightmare.

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Andrew Naughtie

News reporter and author at @websalespromo


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